Family Support

Collage made by Caira for Jon’s birthday

When I made the decision to leave the United States and become an expat in Nicaragua, I knew the most difficult part was going to be leaving my family. The most painful goodbye, specifically, would be with my little sister Caira. We have a sibling connection that has grown into a close relationship that we both cherish. We’ve been through a lot together and I was concerned about how she would take my big move. But I knew I had to follow my dream. I truly believed that pursuing my new life would not only allow me to grow, but it would also enable those close to me to grow as well.

Caira recently wrote a memoir for school exposing what she was thinking in the final hours before I left California to live in Nicaragua. I am very proud of her and thankful for her support as I become an expat. 

I feel my eyes fill up with tears. My throat is tightening. I’ve never been good with goodbyes. But this time was different. My brother, my inspiration, my mentor was leaving. Packing up and moving, out of town, out of state, out of country.


I desperately wanted to grab on to him and beg him not to go, but I knew that wasn’t the right thing to do.


My family had been torn apart since I was 9. He was the one who took me trick-or-treating that Halloween. I’ll never forget it. He dressed up in an Eeyore costume and walked me door to door. My big brother at that point had become a new father figure to me. I knew that no matter what I was going through, he would always be there for me.


And now I have to say goodbye. Give him one last hug on a street corner in SF and wish him luck. Because as much as I am struggling to let him go, I am so proud of him. My big brother, the only person who made me believe that the male gender wasn’t all trash, was moving to Nicaragua to fulfill his dreams. To start a business that will better the world. And in my opinion better him, if that is at all possible.


Tears are now streaming down my face as he gives me a final squeeze. I climb in my car and give a sad wave as I pull away. But I know it’s time. I’m 18 years old and I will be just fine without him. It is now my turn to help my big brother. He needs my admiration and support if I want him to succeed at living his dream, and truly live his Life Out of the Box.

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